Phenyl-1,2,4-Triazol-3-yloxyacetoxy Alkylphosphonates IK

General procedure To a stirred solution of the appropriate (9,(9-dialkyl l-(chloroacetoxy)alkylphosphonates M3 (0.01 mol) in 50 mL of dry acetonitrile, sodium salt of l-phenyl-3-hydroxy-l,2,4-triazole M7 (0.01 mol) and tetrabutyl-ammonium bromide (0.4 mmol) were added at room temperature. The mixture was stirred at 40-50 °C for 4—5 h. The solid was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and eluted with petroleum ether/acetone (2/1, v/v) to give the corresponding pure IK as yellow crystals or a sticky yellow liquid. A series of IK could be obtained by this procedure in yields of 66-85 % [19]. 

The structures, physicochemical data, and yields of IK are listed in Table 9.13. 

10 Alkali Metal Salts of 0-Alkyl Alkylphosphonic Acids IIA-IIE 

General procedure A solution of the appropriate 0,0-dialkyl 1-(substituted phenoxyacetoxy)alkylphosphonate (0.02 mol) and oven-dried lithium bromide, sodium iodide, or potassium iodide (0.02 mol) in dry acetone (molecular sieve 4 A, 40 mL) was refluxed with stirring under nitrogen for 2-22 h. The solution was evaporated under reduced pressure. The residual solid was reciystallized from dichloromethane to afibrd corresponding pure product as a white solid or ctystal. IIA-IIE could be obtained by this procedure in 43-88 % yields and these alkali metal salts were easily deliquescent in air [20-23]. 

General procedure Under a nitrogen atmosphere and in a dark environment, to a solution of appropriate 0,0-dimethyl 1-(substituted phenoxyacetoxy)alkylphosph-onate lA or IC (10 mmol) and sodium iodide (22 mmol) in acetonitrile (25 mL), trimethylchlorosilane (22 mmol) was added at 30 °C. Then the reaction mixture was stirred at 30 °C for 1-2 h. The mixture was filtered and washed with petroleum ether. The solution was evaporated at reduced pressure to afford corresponding 

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